Chemo-enzymatic Synthesis of Halogenated Hapalindole-type Alkaloids

Sosa, Yelissa (2019) Chemo-enzymatic Synthesis of Halogenated Hapalindole-type Alkaloids. Master's Thesis, University of Pittsburgh. (Unpublished)

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Abstract

Halogenation of natural products have been achieved through chemical or enzymatic approaches with some limitations such as selectivity and multiple steps. To circumvent these limitations, we have coupled both approaches by utilizing the Horner-Wadworth-Eammon (HWE) reaction, a prenyl transferase and an isomerocyclase that originate from cyanobacteria strains, to generate seven halo-substituted 12-epi-fischerindoles. The crystal structure of the prenyl transferase was also used to gain insight on the promiscuity of this enzyme and aided in the optimization of the enzymatic synthesis of halo-substituted 12-epi-fischerindoles.

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Details

Item Type:	University of Pittsburgh ETD
Status:	Unpublished
Creators/Authors:	Creators Email Pitt Username ORCID Sosa, Yelissa yas44@pitt.edu yas44
ETD Committee:	Title Member Email Address Pitt Username ORCID Committee Member Islam, Kabirul kai27@pitt.edu kai27 Committee Member Childers, Seth wschild@pitt.edu wschild Committee Chair Liu, Xinyu xinyuliu@pitt.edu xinyuliu
Date:	30 September 2019
Date Type:	Publication
Defense Date:	30 April 2019
Approval Date:	30 September 2019
Submission Date:	7 August 2019
Access Restriction:	5 year -- Restrict access to University of Pittsburgh for a period of 5 years.
Number of Pages:	85
Institution:	University of Pittsburgh
Schools and Programs:	Dietrich School of Arts and Sciences > Chemistry
Degree:	MS - Master of Science
Thesis Type:	Master's Thesis
Refereed:	Yes
Uncontrolled Keywords:	hapalindole, alkaloid, cyanobacteria, halogen
Date Deposited:	30 Sep 2020 05:00
Last Modified:	30 Sep 2020 05:00
URI:	http://d-scholarship.pitt.edu/id/eprint/37352

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• Chemo-enzymatic Synthesis of Halogenated Hapalindole-type Alkaloids. (deposited 30 Sep 2020 05:00) [Currently Displayed]

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